CN111132969B - 作为tlr7激动剂的经取代的咪唑并喹啉 - Google Patents
作为tlr7激动剂的经取代的咪唑并喹啉 Download PDFInfo
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- CN111132969B CN111132969B CN201880057607.XA CN201880057607A CN111132969B CN 111132969 B CN111132969 B CN 111132969B CN 201880057607 A CN201880057607 A CN 201880057607A CN 111132969 B CN111132969 B CN 111132969B
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- alkyl
- butyl
- imidazo
- quinolin
- alkoxy
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- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title abstract description 12
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 title description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- -1 1, 1-dioxothietin-3-yl Chemical group 0.000 claims description 184
- 150000001875 compounds Chemical class 0.000 claims description 161
- 150000003839 salts Chemical class 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 206010028980 Neoplasm Diseases 0.000 claims description 38
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 201000011510 cancer Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 230000002062 proliferating effect Effects 0.000 claims description 5
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
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- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 18
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000872 buffer Substances 0.000 description 15
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
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- 125000001424 substituent group Chemical group 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
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- 239000000741 silica gel Substances 0.000 description 13
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2017/072353 | 2017-09-06 | ||
| EP2017072353 | 2017-09-06 | ||
| PCT/EP2018/073485 WO2019048353A1 (en) | 2017-09-06 | 2018-08-31 | SUBSTITUTED IMIDAZOQUINOLINES AS TLR7 AGONISTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111132969A CN111132969A (zh) | 2020-05-08 |
| CN111132969B true CN111132969B (zh) | 2024-01-30 |
Family
ID=63586658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880057607.XA Active CN111132969B (zh) | 2017-09-06 | 2018-08-31 | 作为tlr7激动剂的经取代的咪唑并喹啉 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US11279684B2 (sr) |
| EP (2) | EP3679025B8 (sr) |
| JP (1) | JP7304848B2 (sr) |
| KR (1) | KR20200050964A (sr) |
| CN (1) | CN111132969B (sr) |
| AU (1) | AU2018329152B2 (sr) |
| BR (1) | BR112020004505A2 (sr) |
| CA (1) | CA3074611A1 (sr) |
| DK (1) | DK3679025T3 (sr) |
| ES (1) | ES2914800T3 (sr) |
| HR (1) | HRP20220669T1 (sr) |
| HU (1) | HUE058995T2 (sr) |
| IL (1) | IL273039B2 (sr) |
| LT (1) | LT3679025T (sr) |
| MX (1) | MX2020002366A (sr) |
| PL (1) | PL3679025T3 (sr) |
| PT (1) | PT3679025T (sr) |
| RS (1) | RS63265B1 (sr) |
| SG (1) | SG11202001926QA (sr) |
| SI (1) | SI3679025T1 (sr) |
| WO (1) | WO2019048353A1 (sr) |
| ZA (2) | ZA202001267B (sr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019040491A1 (en) * | 2017-08-22 | 2019-02-28 | Dynavax Technologies Corporation | MODIFIED ALKYL CHAIN IMIDAZOQUINOLINE TLR7 / 8 AGONIST COMPOUNDS AND USES THEREOF |
| WO2019048036A1 (en) * | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
| CU24679B1 (es) * | 2019-03-07 | 2023-09-07 | BioNTech SE | Proceso para la preparación de una imidazoquinolina sustituida |
| CA3184740A1 (en) * | 2020-07-08 | 2022-01-13 | Purdue Research Foundation | Compounds, compositions, and methods for the treatment of fibrotic diseases and cancer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101980707A (zh) * | 2008-03-24 | 2011-02-23 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451810B1 (en) | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6677349B1 (en) | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| MY157827A (en) | 2003-06-27 | 2016-07-29 | 3M Innovative Properties Co | Sulfonamide substituted imidazoquinolines |
| WO2005051324A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| JP6956070B2 (ja) | 2015-08-31 | 2021-10-27 | スリーエム イノベイティブ プロパティズ カンパニー | グアニジン置換イミダゾ［４，５−ｃ］環状化合物 |
| WO2019048036A1 (en) * | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
-
2018
- 2018-08-31 AU AU2018329152A patent/AU2018329152B2/en active Active
- 2018-08-31 CN CN201880057607.XA patent/CN111132969B/zh active Active
- 2018-08-31 IL IL273039A patent/IL273039B2/en unknown
- 2018-08-31 MX MX2020002366A patent/MX2020002366A/es unknown
- 2018-08-31 KR KR1020207006141A patent/KR20200050964A/ko not_active Application Discontinuation
- 2018-08-31 EP EP18769603.4A patent/EP3679025B8/en active Active
- 2018-08-31 BR BR112020004505-5A patent/BR112020004505A2/pt unknown
- 2018-08-31 RS RS20220493A patent/RS63265B1/sr unknown
- 2018-08-31 EP EP22169256.9A patent/EP4098652A1/en active Pending
- 2018-08-31 SI SI201830679T patent/SI3679025T1/sl unknown
- 2018-08-31 PT PT187696034T patent/PT3679025T/pt unknown
- 2018-08-31 WO PCT/EP2018/073485 patent/WO2019048353A1/en unknown
- 2018-08-31 SG SG11202001926QA patent/SG11202001926QA/en unknown
- 2018-08-31 HR HRP20220669TT patent/HRP20220669T1/hr unknown
- 2018-08-31 CA CA3074611A patent/CA3074611A1/en active Pending
- 2018-08-31 DK DK18769603.4T patent/DK3679025T3/da active
- 2018-08-31 US US16/644,079 patent/US11279684B2/en active Active
- 2018-08-31 HU HUE18769603A patent/HUE058995T2/hu unknown
- 2018-08-31 JP JP2020513788A patent/JP7304848B2/ja active Active
- 2018-08-31 PL PL18769603T patent/PL3679025T3/pl unknown
- 2018-08-31 LT LTEPPCT/EP2018/073485T patent/LT3679025T/lt unknown
- 2018-08-31 ES ES18769603T patent/ES2914800T3/es active Active
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2020
- 2020-02-27 ZA ZA2020/01267A patent/ZA202001267B/en unknown
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2021
- 2021-02-26 ZA ZA2021/01323A patent/ZA202101323B/en unknown
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2022
- 2022-02-10 US US17/669,117 patent/US11987569B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101980707A (zh) * | 2008-03-24 | 2011-02-23 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
| CN103396415A (zh) * | 2008-03-24 | 2013-11-20 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
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